2,2,5,7,8-pentamethyl-2H-1,4-benzoxazin-3(4H)-one | 1145873-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2,2,5,7,8-pentamethyl-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: 2,2,5,7,8-pentamethyl-4H-1,4-benzoxazin-3-one
• CAS: 1145873-63-7
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: RSUKXMZADOZMHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,5,7,8-pentamethyl-2H-1,4-benzoxazin-3(4H)-one 在 三氟化硼乙醚 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到2,2,5,7,8-pentamethyl-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  5,7,8-Trimethyl-benzopyran and 5,7,8-Trimethyl-1,4-benzoxazine Aminoamide Derivatives as Novel Antiarrhythmics against Ischemia−Reperfusion Injury

  摘要：

  6-Hydroxy-5,7,8-trimethyl-benzopyran derivatives and 5,7,8-trimethyl-1,4-benzoxazine analogues substituted by the lidocaine pharmacophore aminoamide functionality at C4 of N4, respectively, were synthesized and evaluated against arrhythmias associated with ischemia-reperfusion injury. The antiarrhythmic effect of substitutents at positions C2 and C6 was examined. Six out of the 11 new derivatives, exhibited arrhythmia scores 1.0-1.3 versus the control (4.5 +/- 1.2), which was also reflected to the % premature beats (0.5-3.9), control (13.7 +/- 3.6). Selected compounds were further studied by a conventional microelectrode method. 2-diethylamino-1-(5,7,8-trimethyl-2-phenyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethanotic (50) and the trolox-inspired 4-(2-diethylamino-acetyl)-2,5,7,8-tetramethyl-3.4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (62) Suppress reperfusion arrhythmias and reduce malondialdehyde (MDA) content, leading to a fast recovery of the heart after ischemia-reperfusion. They exhibit combined class IB and class III antiarrhythmic properties, which constitutes them as promising compounds for further studies because, due to their multichannel "amiodarone like" effect, less proarrhythmic complications can be expected.

  DOI：

  10.1021/jm801228h
• 作为产物：
  描述：

  2-methyl-2-(2,3,5-trimethyl-6-nitrophenoxy)propanoic acid ethyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以85%的产率得到2,2,5,7,8-pentamethyl-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  5,7,8-Trimethyl-benzopyran and 5,7,8-Trimethyl-1,4-benzoxazine Aminoamide Derivatives as Novel Antiarrhythmics against Ischemia−Reperfusion Injury

  摘要：

  6-Hydroxy-5,7,8-trimethyl-benzopyran derivatives and 5,7,8-trimethyl-1,4-benzoxazine analogues substituted by the lidocaine pharmacophore aminoamide functionality at C4 of N4, respectively, were synthesized and evaluated against arrhythmias associated with ischemia-reperfusion injury. The antiarrhythmic effect of substitutents at positions C2 and C6 was examined. Six out of the 11 new derivatives, exhibited arrhythmia scores 1.0-1.3 versus the control (4.5 +/- 1.2), which was also reflected to the % premature beats (0.5-3.9), control (13.7 +/- 3.6). Selected compounds were further studied by a conventional microelectrode method. 2-diethylamino-1-(5,7,8-trimethyl-2-phenyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethanotic (50) and the trolox-inspired 4-(2-diethylamino-acetyl)-2,5,7,8-tetramethyl-3.4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (62) Suppress reperfusion arrhythmias and reduce malondialdehyde (MDA) content, leading to a fast recovery of the heart after ischemia-reperfusion. They exhibit combined class IB and class III antiarrhythmic properties, which constitutes them as promising compounds for further studies because, due to their multichannel "amiodarone like" effect, less proarrhythmic complications can be expected.

  DOI：

  10.1021/jm801228h

文献信息

• Simple and Efficient Method for the Halogenation of Oxygenated Aromatic Compounds
  作者：Theodora Calogeropoulou、Eftychia Koini、Nicolaos Avlonitis

  DOI：10.1055/s-0030-1260792

  日期：2011.7

  An efficient and mild method for the chlorination and bromination of oxygenated aromatics, with good regioselectivity and excellent yields, using a combination of HX/H 2 O 2 /AcOH in petroleum ether is presented. The effect of ultrasound was investigated.

  提出了一种在石油醚中使用 HX/H 2 O 2 /AcOH 的组合对含氧芳烃进行氯化和溴化的有效和温和的方法，具有良好的区域选择性和优异的收率。研究了超声波的影响。